Yosuke in Alice's Wonderland
by Cold Freezer
Summary: Yosuke thought that the day of the cross-dressing pageant would be the worst day of his life. But can the events that transpire afterwards change his mind?


**Yosuke in Alice's Wonderland. **

* * *

The school day was finally over! This had been, without a doubt, the most embarrassing day in the life of Yosuke Hanamura. He had entered a cross-dressing pageant at school today. That's right, the entire school had seen him in a girly school outfit. The day was going to get better soon, though…hopefully.

You see; Yukiko Amagi, one of his best friends, had invited him and the rest of the group to stay at her family's inn for the night. With a little luck, he and his friends might catch a glimpse of the girls in a bathing suit, just like they had done at school today during the beauty pageant.

Yosuke and Teddie, who lived with Yosuke's family, were packing their things for the night they were going to spend with their friends at the Amagi Inn. Yosuke watched Teddie from the corner of his eye. ''Ted, why are you still wearing your outfit from the pageant?'' he asked, and he quickly sighed when he remembered the things that he had to put up with today. ''I'm scarred for life, dammit,'' he whined.

''What's wrong, Yosuke?'' Teddie asked in his girly voice while whimpering with his eyelashes. ''Is my forbidden flesh too unbearable for you?''

Yosuke rolled his eyes. ''Get real, Ted.'' Still, if you looked just right, Ted looked just like a gir- _'Ah! Trap, trap, trap!' _he quickly reminded himself as he turned off his brain before it could think of something really, really bad.

''Yosuke, have you seen my red rose?'' Teddie asked as he hastily walked through the room, searching for his trademark flower. ''I know I took it home from school.''

''Maybe you left it downstairs,'' the teen suggested.

Teddie quickly ran down to the living room, and Yosuke shut the door behind him. Rise, Chie, and Yukiko had all flaunted their bodies for the pageant, and their barely clothed forms were still fresh on his mind.

He sat down on his bed and lowered his pants and underwear. His member was already hard, and he lowered the skin off his tip with ease, showing his pinks glans that was already surrounded with pre-cum.

The door was slammed open. ''Found it! Turned out that you were ri-'' Teddie stopped right in his tracks, and his bright blue eyes widened from the sight before him. ''Yosuke?''

''T-Teddie!'' the awkward boy stuttered as he clumsily tried to pull his pants back up.

''Yosuke, you're so impure!'' Teddie scolded. ''You should be more like Sensei.''

''Sh-Shut up!'' Yosuke said as his face painted red in shame of getting caught.

Teddie started to chuckle. ''So, tell me: Were you thinking of my fabulous appearance?''

''Of course I wasn't,'' Yosuke snapped, hastily throwing his arms around in the air.

''Geez, don't get mad, Yosuke,'' Teddie started, ''Lots of boys found it unbearable that I'm out of reach.''

''For your information, I was thinking about the swimsuit competition.'' The Junes employee blurted out.

The two went back to packing after this, an uncomfortable silence in the air. Teddie turned to his friend. ''Hey, Yosuke.''

''Yeah?''

''Have you ever scored with a girl before?'' Teddie asked. He had a pretty good idea on what score meant nowadays.

Yosuke sighed. ''Nope.''

Teddie watched his friend, who was currently sulking on the bed. The Shadow had found himself thinking about Yosuke's 'actions' ever since they'd returned to packing. ''Want to score with me?'' he suddenly asked.

Yosuke watched his friend with bewilderment. His friend, that currently looked like one of the cutest girls he'd ever seen, had to be joking…right? He wanted to say no, but quickly found out that he couldn't. Why couldn't he say no?

Teddie was starting to walk towards him. _'Say no! Say no!' _The teen couldn't do it, though. His with hormones filled teenage mind had already decided that Teddie was currently feminine enough for him and had also decided that he was too curious to find out how 'it' felt to stop now. The cross dresser got on his knees and unbuttoned the Persona-user's pants.

''Let's see what pops out,'' the shadow said, much to Yosuke's embarrassment. However, all of his discomfort didn't matter anymore the minute the cosplayer started to slowly dance his tongue around the tip of Yosuke's member. The Junes employee groaned and some blood flew to his cheeks after he realized that, from his position, it really looked like a cute girl was taking him in his mouth. Teddie closed his lips around the tip and started to stroke the teen's shaft. The Shadow slowly took in more and more length, and was forced to take Yosuke in to the hilt when the moaning teen pushed his head down completely. Teddie's long blonde hair fell down with him, and Yosuke used his free hand to hold it away from the cosplayer's face.

The Yasogami High Student's head flew backwards with pleasure; and he started to swing his hips up and down, fucking the Shadow's wet mouth with his manhood that had now started throbbing. It soon became too much for him, and he felt a recognizable feeling creep up through his urethra that he normally only felt when he touched himself. ''Here it comes,'' he groaned out as he released Teddie from his grasp, who quickly withdrew his mouth just before Yosuke released his white fluids.

''Wow…'' Yosuke reflected. ''So that was a blowjob.''

''Congratulations on scoring, Yosuke.''

Both were curious to go further now. And, despite knowing that this was wrong, it was too late for Yosuke to stop. Teddie stood over him, and Yosuke tried to keep himself from looking under the boy's skirt, no matter how much he looked like a cute girl.

The Shadow lowered his panty—he takes cross-dressing very seriously— and rolled the fabric down his soft, hairless, and thin legs. Meanwhile, Yosuke lubricated his tip with his remaining cum. The Shadow was about to take off his dress, but Yosuke protested. ''Then you look too much like a boy,'' he reasoned.

With a sigh, Teddie lowered his dress again before he spread his two butt cheeks apart and lowered himself against the teen's musky tip. ''Like young love on a cool summer night. Two people are about to become one. One, a young innocent boy from another wo-''

''Could you just do it!'' Yosuke screamed, both irritated and impatient.

''Ah, but it's a beary good story…'' he muttered before he slowly but surely lowered himself. It really was a tight fit and the stretching was enormous, but it was working, he was slowly taking Yosuke inside his entrance. Teddie had to give it to the other boy. Yosuke, despite going crazy from the feeling of his member getting squeezed tightly from every direction, never moved a muscle, only roaming his hands over the cosplayer's soft thighs.

The pain was slowly subsiding; and Teddie started to move a bit, lifting up and sinking down tenderly. He set a slow rhythm, going up almost all the way and then slowly sinking down again. He had never felt such friction against his inner walls before; it was definitely an experience, he decided.

But it seemed like he wasn't fast enough for Yosuke's taste because, when he started to sink down the next time, the teen gave in to his pleasure and suddenly bucked his hips up, surging into the cosplayer with a hard thrust.

''Aaaaah!'' the Shadow screamed, he felt like he was getting ripped apart! He clutched his hands tightly against the blue lining of his skirt.

Both moaned and groaned as Teddie bobbed his body. The Shadow could feel his own seeds rising and knew that all he needed was some stimulation. He pulled his dress up and started to stroke his dick. ''H-Hey!'' Yosuke quickly protested. ''You're making it weird!'' He only realized that it had already been pretty weird in the first place after he'd said it.

''Hush, Yosuke, it was just too unbearable!'' The awkward teen closed his eyes and tried to ignore the manhood right in front of him, rather focusing on the narrow hole that went up and down his dick. The tight enveloping of his member soon became too much for his throbbing manhood, and he tightly placed his hands against the other's hips.

Teddie was getting close as well, and stroking his cock while his ass was getting stimulated soon became too much for him; and he let out an animalistic scream as he unloaded himself, scattering his seeds into the air. His climax made the cosplayer's butt cheeks clasp against each other, and Yosuke came from the sudden contraction, jerking his hips up as he discharged himself inside the Shadow.

Teddie panted hard before he collapsed, landing on Yosuke's chest, and his blonde hairs fell over Yosuke's face as he came down. Once they calmed down a bit, Teddie slowly rose himself up, and his manhood and ass became hidden again as his dress fell back down. Teddie winced as the manhood left him, thinking that it would definitely hurt the entire night.

''Crap!'' Yosuke screamed as he looked at the time. ''We need to go to the Amagi Inn.''

''Great!'' Teddie started, ''then we can try to score with the girls.'' He tried to stand but quickly fell back down, the pain immediately eminent as soon as he stood upwards. ''On second thought, I might just do it calm tonight. Honestly, I just don't see what Kanji likes about this.''

Yosuke had a pretty good idea, though.

* * *

**The end!**


End file.
